Selectivity modulation of the Ley–Griffith TPAP oxidation with N-Oxide salts

Peter W. Moore, Yanxiao Jiao, Paul M. Mirzayans, Lexter Ng Qi Sheng, Jordan P. Hooker, Craig M. Williams*

*Corresponding author for this work

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

A wide variety of novel non-hygroscopic N-oxide tetraphenylborate salts were synthesized and evaluated as co-oxidants in the Ley–Griffith (TPAP) oxidation of benzylic and allylic alcohols under non-anhydrous conditions. The novel DABCOO·TPB (2:1) salt was herein unearthed as a viable competitor to the first-generation NMO·TPB (2:1) salt, but more importantly gave increased performance under oxidative competition. X-ray crystal structure analysis and NMR spectroscopy revealed that depending on the crystallization conditions 1:1, 2:1 or 3:2 N-oxide–tetraphenylborate salts could be formed.

Original languageEnglish
Pages (from-to)3401-3407
Number of pages7
JournalEuropean Journal of Organic Chemistry
Volume2016
Issue number20
DOIs
Publication statusPublished - Jul 2016
Externally publishedYes

Keywords

  • Alcohols
  • Oxidation
  • Aldehydes
  • Ley-Griffith reaction
  • N-Oxide salts
  • TPAP

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